Hydrochloric Acid → 3-(3-Methoxyphenyl)indoline

HRID 1489148Notes

Reaction equation

HRID 1489148 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[OH-].[Na+]>[Zn].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 154287153-(3-Methoxyphenyl)indole

Product 1

HCID 154287243-(3-Methoxyphenyl)indolineYield 48.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Ten grams of the abovementioned 3-(3-methoxyphenyl)indole, 700 ml of 6N hydrochloric acid and 300 ml of ethanol were mixed and refluxed while 100 g zinc powder was added in small portions, and then the reflux was continued for 5 hours. The reaction solution was made alkaline with an aqueous sodium hydroxide solution and extracted with chloroform. The resultant extract solution was concentrated to a residue which was then dissolved in diluted hydrochloric acid, and washed with ether. The aqueous layer was made alkaline with sodium hydroxide, extracted with chloroform, and dried and concentrated to obtain 4.9 g of 3-(3-methoxyphenyl)indoline.

Workup

  1. additionwas added in small portions
  2. extractionextracted with chloroform
  3. extractionThe resultant extract solution
  4. concentrationwas concentrated to a residue which
  5. dissolutionwas then dissolved in diluted hydrochloric acid
  6. washwashed with ether
  7. extractionextracted with chloroform
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a8eafaad19b74b64894cde9c44c7ffbc
Source dataset
uspto-grants-1997_10
Patent number
US05677326

Reaction notes

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